Two Bet's Don't Make A Right
by hbarker10
Summary: When 26 year old History student Derek Hale asks 18 year old English student Stiles Stilinski out his friends bet him that he won't be able to go 2 months without sleeping with Derek. Never one to back down from a challenge Stiles accepts the terms and goes about to prove them all wrong. But what happens when Derek's intentions with Stiles aren't all that innocent?
1. 13th October

13th October

Stiles was confused. I confused the right word? Maybe surprised was a better word. He walked along his usual route to meet his friends and tried to wrap his head around what just happened.

_20 minutes earlier…_

_ "Stiles!"_

_ "Stiles, wait up!" Stiles stopped and turned to face a very flushed Derek Hale. "Did you not hear me shouting you? I've been running after you for like 10 minutes."_

_ "No yeah I heard you."_

_ "Oh." Derek looked a little put off but he quickly recovered as he threw his best smile at Stiles. "Listen, I was wondering if maybe you wanted to go out to dinner tomorrow night."_

_ "What?"_

_ "Dinner. With me. Tomorrow at 8."_

_ "Er…sure." Derek had smiled at him and then just turned around and left Stiles standing shocked and well…confused._

So it was safe to say that Stiles had no idea what just happened. Sure he had a crush on Derek; I mean who wouldn't, he was tall and had muscles on his muscles and his face was all chiselled and stubble. It was just before today Stiles had spoken to Derek for all off one time and that was at Lydia's party a month ago. Stiles had been trying to find the bathroom in Lydia and Allison's apartment and he'd come across a bedroom instead; he'd found Derek on his back with a girl on top of him. Derek looked pretty out of it so Stiles thought it would be best to break up the little party, the girl had grumbled and slapped him but Derek was pretty grateful. Apparently Derek had just been dumped, so he drank more than he should, and that had been his ex who he did not want to sleep with. Stiles had listened and helped Derek home but they'd never spoken again and Stiles knows that had Derek been sober the information would never have been so freely offered. He just couldn't wrap his head around the whole thing, probably better for him to just ask his friends what they thought. He pushed in to the coffee shop and was instantly hit with the aroma of coffee. He shivered a little as the heat of the coffee shop hit him and smiled as Scott waved him his coffee at him. Ah Scott was the greatest best friend.

"Ah Scott why couldn't we fall in love and be together forever." Scott smiled as Stiles wrapped his hands around the cup and took a sip.

"Well I'm just guessing but it could be because you have a date with Derek Hale." Stiles spluttered a little as Lydia smirked over the edge of her cup.

"That literally just happened!"

"It happened about 23 minutes ago and you should have text me as soon as it did."

"Well I was on my way here so I didn't see the point."

"Did you say yes? Who am I kidding; of course you did, a straight man wouldn't turn down Derek Hale."

"Whoa, I would never say yes to Derek Hale."

"Scott you don't count you're not gay or straight, you're Allisonsexual." 3…2…1and there's the Allison look.

"Lydia it doesn't matter okay, its one date and then we'll never go out again." Lydia raised one perfectly sculpted eyebrow at Stiles then pursed her lips as she thought about what to say next. She was about to speak when Jackson interrupted by joining them.

"Stiles I hear you're finally gonna get laid."

"I'm sorry what?"

"Well Lydia told me about your date with Derek and we all know about the massive hard on you have for him so as off tomorrow night you will no longer be a virgin."

"Then you're all wrong because there is no way I am sleeping with Derek Hale tomorrow night." Stiles turned to glare at Scott and Allison as they tried to hide their laughter in each other's necks.

"Stiles I'm sorry but come on you talk about losing your virginity all the time and Derek's been known to take quite a few."

"Oh my god it is not gonna happen."

"Stiles it's not that we don't believe you, it's just Derek can be really persuasive and I love Scott but Derek's really hot." Allison instantly ran her hands down Scott's back as he whined at her words.

"I can't believe none of you believe me, I bet I could last atleast a week!"

"Oh honey, if you're gonna make a bet atleast make it interesting."

"Interesting how?"

"If you can go two whole months without sleeping with Derek then you can have the spare room in my apartment."

"But you and Danny said I wasn't allowed to because I was annoying."

"You're still annoying but I doubt I'll lose so…"

"Wait what do you want if I lose?"

"You have to wear whatever Lydia tells you too for a whole week."

"That's it?!"

"Wow Jackson that is weak."

"Your call Stilinski."

"Fine. You guys are on. I win I get Jackson's spare room; you win Lydia gets to dress me. You guys are witnesses to this so Jackson can't go back on his word. Okay?" Everyone nodded round the table and smiled at Stiles as he pushed back from the table.

"I gotta go to class. This is not over." Stiles stormed out of the coffee shop and everyone watched him go until he rounded the corner and was no longer in sight. They all turned to each other and Lydia was the first to talk.

"So what are the in house bets?"

"Stiles is my best friend so I have to be nice, I'm gonna say $20 on 2 months."

"Okay, well it's Stilinski so $20 on a week. And Danny says $20 5 weeks."

"Well I love Stiles but I really don't think he'll last two months, so I guess $20 on a month. Lydia?"

"I actually have a little faith in his complete and total stubbornness so $20 on a month and a half."

Jackson clapped his hands together and smiled at everyone. He was totally going to win this and Stilinski had no idea what kind of clothes he was going to be wearing.


	2. 14th October

14th October

"It's a date with Derek Hale Stiles."

"Fine, I'll change my shirt."

"And…"

"The pants."

"Wear the black jeans I got you and the dark blue shirt I know Allison got you for Christmas."

"You know I can't actually remember asking for your help."

"I know, really Stiles what were you thinking?" Stiles huffed and rummaged around his wardrobe for the preferred clothes.

"I can't find them."

"Are they hanging up?"

"Oh hey would you look at that?" The group rolled their eyes collectively as Stiles changed his clothes; they were all currently sat on his bed watching The Notebook. Lydia and Jackson had the laptop resting on their knees while Scott and Allison were trying to climb in to each other's mouths. Danny was in the middle of both couples looking like he was about ready to swat Scott and Allison apart.

"Okay, how do I look?" Stiles spread his arms out and even Danny couldn't resist giving him an appreciative whistle. Stiles smiled and pulled on some shoes before everyone froze as a knock came to the door. Stiles looked up to everyone and he half considered breaking out through the window.

"What time is it?" Danny looked down at his watch and smiled at Stiles.

"Just turned 8. Guess that must be your prince charming now." Stiles hurried to the door before anyone could get to it before him. He pulled it open to Derek with his fist half way to the door, he looked Stiles up and down then smiled as he dropped his hand.

"Hey, you ready?"

"Yeah. Just let me grab my keys and phone." Stiles edged the door closed and grabbed his stuff from Lydia's hand.

"What are you guys gonna do?"

"We were gonna go back to Jackson's, but don't worry Scott has a key so we'll just lock up after you've gone."

"Right. Good. Okay. Bye." Stiles stepped out in to the hall with Derek and smiled as they started walking down the hall. Stiles had never had a problem filling silences but right now it was a little…okay a lot awkward. He doesn't remember this part in the movies, it was always pick them up, smile, and then next shot there in the restaurant having eye sex and conversation, nobody mentioned the pre-dinner awkward pick up.

"So you do History right?"

"Yeah, I'm on my second year though."

"Do you like the course?"

"Yeah it's good, I always liked the subject at school and I guess I never really wanted to do anything else."

"Cool."

"What is that you take?"

"I do English, I mean I liked most of my lessons at school but I want to be a teacher so it seemed like the best choice."

"What age do you want to teach?"

"Like kindergarten or maybe 1st grade."

"That's really cool Stiles." Derek pushed open the door to Stiles building and walked towards his car.

"Dude, is this your car?"

"Well it used to be my sisters, but yeah its mine now."

"It's gorgeous!"

"Thanks. Do you actually want to get in it, or just stare at it?"

"I'm debating." He threw Derek a smirk over the roof of the car and then pulled open the door and climbed in. Derek joined him moments later and he started the car up.

"Where exactly are we going?"

"Restaurant in town."

"Any further details you want to share?"

"Nope."

"Is it expensive, because I don't have a lot of money?"

"I'm paying, don't worry about it."

"Dude, I really don't mind paying for myself."

"Stiles I asked you out, it's okay." Derek gave Stiles a small smile and put his hand on Stiles's knee. Stiles tensed slightly and Derek glanced at him with a worried expression.

"Is this not okay?"

"No. I mean yes. It's fine honestly." Stiles tried to give Derek a reassuring smile but it felt more awkward than anything. Come on Stiles he's touching you knee not your dick. As long as there is no sex tonight or any night for the next two months everything will be fine. Oh god why is this so hard all of a sudden…now is not the time to think about things getting harder.

"Erm…Stiles?"

"Yeah?"

"Any reason you're mumbling about things getting harder?"

"Er…I just meant in this weather, getting harder to see the road."

"It's a clear night."

"Right. I was just testing you; you know road safety and all." Stiles turned towards the window and tried to hide how red his cheeks were. Derek squeezed Stiles knee a little and concentrated back on the road. Stiles tried to will his blush away before they got to the restaurant. Unfortunately for Stiles they pulled in to the parking lot 5 minutes later and his blush was still going strong. He got out of the car and met Derek round the front.

"Stiles are you okay? You seem nervous."

"Its just I've never actually dated anyone before, so I guess I am a little." Derek laced his fingers through Stiles's and squeezed reassuringly.

"Let's just worry about what to order first." Stiles smiled and let Derek pull him towards the door of the restaurant. Stiles squinted as they walked inside; the place was lit by a few over head lights and candles on every table and Stiles had never been somewhere so romantic. Derek seemed to know what he was doing though; the hostess knew his name and told him to take his usual table. How often did he do this? Derek pulled out Stiles's chair for him and Stiles smile just felt weird on his face.

"So come here often?" Derek cursed under his breath as he banged his elbow of the corner of the table.

"I'm sorry?"

"You just seem to know your way around the place."

"Oh. Yeah I used to work here."

"Oh, cool." Stiles let out a sigh of relief as the waitress came over and handed them each a menu. Derek ordered them two cokes and Stiles just smiled politely as she glared at him a little.

"Did you date anyone that works here?"

"Yeah. Jennifer."

"I'm gonna take a stab in the dark here and say she's our waitress."

"Yeah, do you know her?"

"No but she's still glaring at me, so yeah."

"Do you want to leave? If she's making you uncomfortable…"

"Oh Derek no, it's kind of funny that she hates me for just going on a date with you." Derek slid his hand across the table to link with Stiles's fingers.

"Well maybe we should give her something to really glare about."

"What did you have in mind?" Stiles swallowed a little at the mischievous glint that seemed to come in to Derek's eyes. Derek stood up and Stiles felt a little panic run through him as it looked like Derek was about to bail, but instead he came round the table and stopped at Stiles side. Stiles eyes couldn't seem to leave Derek's and his breath came out a little ragged as Derek dragged his hand up Stiles arm to his neck and he bent closer to Stiles. Derek's mouth was inches from Stiles's and he felt Derek exhale as he spoke barely above a whisper "Do you want me to stop?" Stiles did not so instead of answering he moved the last few inches and brushed his lips against Derek's. Derek knew that was the only answer he was going to get so he put a bit more in to the kiss. Stiles had been expecting fireworks and maybe something monumental but somehow this was better, it was real. It felt like it lasted hours but it was nothing more than 30 seconds before Derek was pulling back. His eyes seemed a little darker and he put a smirk on his face like he knew he was affecting Stiles, because he was, but that didn't mean that Stiles couldn't see he'd affected Derek as well. Derek moved back to his seat and Stiles jolted a little as Jennifer practically slammed the drinks on the table, he'd almost forgotten the reason for Derek kissing him.

"Do you want food?"

"Please."

"Then order something."

"I shall have the meat pizza please, Stiles?"

"I'll have the Bolognese please."

"Would you like extra garlic with that?"

"No thanks." Jennifer picked up the menu's and stormed back towards the kitchen to give in their order.

"You know she probably spit in our drinks right?" Derek eyed the drink suspiciously before taking a big gulp of it; he swallowed it down and made a loud 'Ahhhh' sound.

"Well that is some good coke, maybe she should spit in all the drinks." Stiles couldn't help but snort at that and he hid his face behind his hand a little as though he could hide the sound. Derek just chuckled and hooked his ankle around Stiles's. Dinner went better after that, the kiss had taken away some of the awkwardness and they maintained none awkward conversation where Stiles didn't even embarrass himself. Jennifer had brought their food, probably spit in that too, but they just ate and murmured their enjoyment much to her dismay. Afterwards they just settled in to an easy conversation and they didn't even realise how long they'd been sat there till Jennifer came over and told them to get out. Whatever, she looked frumpy in that shirt. It wasn't until they were back in the car and on the way to Stiles's flat that Stiles remembered he couldn't have sex with Derek tonight. No sex for him or he would have to wear what Lydia told him too and with the influence of everyone else it could be something completely ridiculous. Crap. Stiles swallowed as Derek pulled up outside his building.

"So I had a great night, thanks Derek."

"You don't want me to come upstairs?"

"Nope. But I would like to do this again if you want to?"

"You're just going to go inside alone?"

"Yes Derek. Wow you do not get turned down on the first date often do you?"

"More like never."

"Well there's a first for everything." Stiles leaned over the dash and gave Derek a quick kiss on the lips before he jumped out of the car. Derek was still staring a little dazed at Stiles as he walked away. He watched as Stiles turned around to give him a little wave then walked inside his building. Derek was only broken out of his stupor when his phone blared out against the silence of the car. He forced it out of his pocket and answered.

"Why are you answering?"

"Gee Erica maybe because you rang me."

"No you idiot why aren't you with Stiles?"

"I was, he just got out of the car."

"And you didn't go with him?"

"He didn't want me to."

"What?"

"He didn't want me to go up."

"Wait, are you telling me that Stiles turned down your offer of sex?"

"Yes." Derek glared at the phone as Erica started to cackle down the phone, he started saying her name till she finally took some deep breaths and apparently got herself under control.

"Wow, and you thought it would be so easy."

"I thought it would be!"

"Oh Der, you know you only win the bet if you actually sleep with him right?"

"Yeah I know." Derek hung up the phone and sat in his car for a few minutes before he actually started her up. Clearly a romantic restaurant was the wrong direction, okay time to think of a new plan.


	3. 16th October

16th October

"Have you called him yet?"

"No Erica, he was too busy diving out of my car to give me his number."

"So then why are you sat in your living room, in your boxers?"

"My ego has taken a hit, let me wallow in self-pity." "

Derek, it was two days ago get over it and you're never going to win if you sit here and mope." "Wallowing not moping."

"You're an idiot. Now get up and go get his number!"

"I don't know where he is." Erica folded her arms over her chest and stared at him until Derek huffed then pushed himself up.

"Fine I will go and get dressed and then go out, and if I happen to come across him then fine." "Happen to? Really Der, we both know you're going to actively look for him."

"Whatever Erica, I just want to win." Derek made a wide gesture with his hands and then left the room to Erica's disapproving stare. He was going to win; he just needed to try a little harder when it came to Stiles. He looked through his closet and decided he just needed to show Stiles what he was missing. His tightest jeans had never failed him and his tight black t-shirt did wonders for his arms. "Erica?" She sauntered in to his bedroom and flopped down on to his bed. She frowned as she pulled his jeans out from under her.

"Oh wow, you're really going all out for this."

"Shut up I clearly need the help."

"Derek honey I've told you if you keep wearing these pants you will never have children."

"I will deal with that later for now I really need to find Stiles."

"Did you call me in here to watch you dress because I've told you that doesn't do it for me."

"No. I wanted to get your approval on the outfit."

"Oh okay, this would probably work better if you were wearing it."

"Right. Turn around."

"Seriously?"

"Yeah I need to change in to briefs if I'm gonna wear those jeans." Erica rolled her eyes but turned around regardless. Derek quickly pushed his boxers down and pulled up his briefs before Erica could even peek.

"You realise I've seen you shower right?"

"What? No you haven't!"

"Oh really then how do I know about that freckle on your left butt cheek?"

"What freckle, I don't know what you're talking about."

"Sure you don't Derek." Erica turned and winked at him. Derek grabbed his t-shirt off the bed and pulled it over his head before picking up his jeans. He looked between Erica and the jeans a few times before asking.

"Can you help me in to these…please?"

"Don't act so shy Der, I'm your best friend, I've seen you in much worse scenarios than me helping you get those tight ass jeans over your thighs." Erica walked round behind him and Derek pulled the jeans over his feet till they bunched up at his ankles. Erica squatted down and grabbed them and pulled them till she felt the resistance just over his knees.

"Derek did you put more muscle on?"

"I may have done more leg workouts at the gym."

"Urgh you couldn't just work out your upper body."

"No." Erica grabbed the top of the jeans and pulled them up as far as she could.

"Derek I need you to like pull your ass in."

"Are you serious?"

"Yeah." Derek huffed and tensed his ass a little to try and make it smaller as Erica gave the jeans one final pull and they both relaxed a little as they went up. They both whipped their heads round as someone cleared their throat from the door. Boyd was leaning against the door frame with his arms over his chest as he looked at them.

"What you've never seen a grown man get help with his jeans before?"

"No I have. However the frequency of which you are that man is troubling."

"It's not that often!"

"4 times last week."

"I had a busy week."

"You stayed in 5 times last week."

"That's not true, I went out and did stuff."

"Derek it's okay. We know you just like wearing the pants."

"They make my ass look great."

"Sure. Tell you what Derek if you can zip them up right now I'll give you 10 bucks."

"You want me to do it right now?"

"Without sucking in or Erica's help." Derek huffed then made a show of grabbing the top of his jeans and pulling them together. He tried to bring the tops together but he couldn't quite get them together, he smirked over at Boyd then squared his shoulders a little and tried again but he just couldn't get them to meet.

"I don't need to prove anything to you!"

"I'll be in the kitchen." Erica blew him a kiss and turned back to Derek.

"Okay let's get those pants up!"

Derek had been walking around the campus for nearly an hour. He'd been to all the places he had seen Stiles and his friends hang out, they were a pretty noticeable group, but he hadn't been able to find them anywhere and his pants were literally about to cut off his circulation, breathing was difficult at this point. Seriously why is it that when you're not looking for something it's always there but the minute you actually want it it mysteriously disappears. He pulled his phone out of his jacket pocket and called Erica.

_"What?"_

_"I can't find him."_

_"Derek I am a little busy."_

_"I'm serious Erica, get off Boyd and help me!"_

_"Fine. Did you check the library, the theatre and the coffee shop?"_

_"Yes to all three."_

_"What about the ice rink and the bowling place?"_

_"Yes and no."_

_"So go to the bowling alley. Kay, good, bye."_ Derek pulled the phone away from his ear as the call ended. There was no way he could go to the bowling alley and just pretend to come across them, but what if there not even there. Wait Isaac might be working tonight. Derek dialled Isaac's number and hoped he had his phone on him.

_"Hello."_

_"Isaac, its Derek."_

_"Yeah I have caller I.D, like most people these days."_

_"You're at work aren't you?"_

_"Was it my monotone voice that gave it away?"_

_"Pretty much, listen you are aware of mine and Erica's bet right?"_

_"Yes and yes Stiles is here."_

_"Can you put him on the phone?"_

_"No."_

_"What why?"_

_"Erica said I could help you as long as it didn't prevent you from doing something embarrassing and you coming down here will probably be embarrassing."_

_"Come on who are you more afraid of me or her?"_

_"Before I knew you, you. Now I know you, so her."_

_"Dammit Isaac."_

_"Just get down here Derek."_ Derek glared at the phone as it beeped to inform him the call had ended. Alright walking to the bowling alley, thank god it was only 15 minutes away.

Derek got there in half an hour. Not bad considering how much these pants were cutting in to his balls. He walked in and instantly saw Isaac sat at the front desk.

"I have no other words than wow."

"Shut up I look amazing."

"But can you breathe?"

"A little."

"He's on the 9th row."

"What the hell do I say?"

"I'm sorry Derek Hale doesn't know how to seduce someone in to bed, oh wait that's right he doesn't want to be in your bed."

"You're an asshole and he does, he's obviously not a first date kinda guy."

"Or a Derek Hale kind of guy."

"Just you watch. I'm gonna go over there and score myself a second date and his number."

"Ever thought that maybe there's a reason he didn't give you his number." Derek pursed his lips a little and made his way towards row 9. He could see Stiles and his friends which meant he noticed the minute they saw him. He saw Lydia hit Stiles and he turned so quickly he nearly lost his balance but he righted himself and stared at Derek. Derek gave him a little smile but Stiles just seemed to stare over his shoulder.

"Hey Stiles."

"Derek."

"Is everything alright?"

"Yeah, what do you want?"

"I saw you over here so I came over to ask you out."

"You wanna ask me out?"

"Well yeah."

"Derek you haven't spoken to me in two days, and you just want to come over here and ask me out?"

"Stiles I didn't have any way to get in touch with you."

"What are you talking about I gave you my number."

"No you didn't."

"What? Yes I did. I said I wanted to do this again and then…oh crap."

"Then you jumped out of the car."

"Oh my god, I apologise for all the bad things I said about you in the past two days."

"What did you say?"

"It doesn't matter but I would absolutely love to go on another date with you." Stiles came round the booth and stood in front of Derek before handing him his phone. "Can I have your number please?"

Derek smiled and took the phone from him. He put in his number and then texted himself so he could have Stiles's. Everything went fine for the next 30 seconds, until he handed Stiles his phone back and dropped it in Stiles hand, except the phone just seemed to slip right through his fingers. Derek squatted down to pick it up but the minute he did he felt his jeans finally give under the pressure and the material just couldn't handle it anymore. He felt it split from the crotch and then down the back of his right thigh. He stood up and Stiles was looking at him with a cross between horror and humour.

"Dude did your pants just…"

"Yes. Yes they did."

"Please tell me you drove here."

"Nope." And then Stiles couldn't seem to stop the laughing that bubbled out of his mouth. He heard a camera go off behind him and briefly saw the flash and guessed it was most likely Isaac sending a picture to Erica or putting it on Facebook for his family to see. Stiles's friends quickly followed Stiles and Derek was left standing their looking up to the ceiling asking why me?

"Stiles?"

"Mmmm"

"I will text you tonight. Right now I have to walk home."

"Do you want a lift?"

"No. Consider this karma for not calling you for two days."

"That wasn't your fault though."

"No but I could have come and found you."

"Okay. Then enjoy your walk of shame." Derek gave a final smile to Stiles and then turned on his heel. He saw a brief flash and looked over his shoulder at Stiles; he smiled and waved the phone at him.

"I need a contact picture." Derek laughed a little as he continued on. He walked past Isaac who tried his best not to laugh at him and then walked right out of the building. Sure he had a 40 minute walk home but he got a second date with Stiles. And if all it took to win the bet and sleep with Stiles was embarrass himself a little then Derek could totally deal with walking home in split jeans. This wasn't gonna be so hard after all.


	4. 20th October

**_October 20th_**

Four days and Stiles was thanking whatever deity out there that he'd convinced his dad to get him unlimited texting because he and Derek had done nothing but text. They arranged a date for later tonight but for now they were just happily texting each other. There texts had covered a lot of different subjects. Starting with the simple stuff and then after a drink on Friday Stiles got a little drunk and little more personal.

_16.10 20:34pm D to S: What's your favourite film?_

_16.10 20:42pm S to D: Batman. He's super awesome and has some kick ass gadgets. To make it even better Bale is hot!_

It had gone from normal like that to…

_18.10 00:05am S to D: Deeeeeeerek! I wan dher yoooo _

_18.10 00:09am D to S: Are you drunk?_

_18.10 00:16am S to D: Npppp. Im hernuy fur yooo_

_18.10 00:18am D to S: Go to sleep Stiles._

_18.10 00:27am S to D: Bwt hhhhhhh np sx fur eeee_

_18.10 00:30am S to D: Derk_

_18.10 00:43am S to D: Sweeply_

_18.10 00:54am S to D: Yo shiudl rake yy visce ndd sweelp_

And Stiles honestly could have punched himself in the face when he opened his new texts on the 19th because there was no way he was entering the real world after drinking that much. According to Lydia though he wasted his day by sleeping and Stiles counteracts with he had the best day by sleeping!

_18.10 13:06pm D to S: So I think I've managed to decipher some of your texts and I believe you want to be under me?_

_18.10 13:06pm D to S: Still horny for me Stiles?_

_18.10 13:08pm D to S: You know I might want to be under you?_

And Stiles had just laughed because Derek didn't make it weird, or atleast weirder, he just went with it and wasn't actually put off by Stiles and his texting habits. So yeah Derek was good and nice, and Stiles really fucking wanted to have sex with him because he was really fucking hot. But he also really did not want to live in dorms next year so he had to win this bet and he had exactly 7 weeks left. Stiles thumped his head down on the table in front of him and for about the hundredth time this week asked what the hell he was thinking with this bet. Stiles stopped banging his head when someone sat down and cleared their throat. He looked up at Lydia.

"Yes?"

"What are you doing?"

"Why did I make the bet?"

"Because Jackson had something you wanted. And when someone has something you want you find a way to get it."

"I know that but I want to sleep with Derek."

"And you can in 7 weeks."

"Lydia there is no way he will wait that long."

"You might not need to wait that long."

"What do you know?"

"Hmmm?"

"Lydia we've been friends for years, I know you and I know when you know something."

"I made a new friend."

"And who is it?"

"Her name's Erica Reyes."

"Yeah I know her, she Derek's friend."

"He's in this for a similar reason to you."

"WHAT?!"

"He may have also made a bet with Erica and she really wants to win."

"So she told you to tell me."

"Yes but I didn't tell her anything about this bet. So as far as she knows I'm just informing you that Derek bet he could get you to sleep with him in two months."

"What an asshole! I've been sat here thinking he's a nice guy, I'm gonna punch him in the balls."

"Or…"

"Or…"

"Stiles you have to go the next two months without sleeping with him. If you do you get the room, if you break it off then the bet is off. Don't dump him, show him you deserve respect."

"When you say respect you mean crush him right because I'm happier with that."

"He has to sleep with you in two months, make sure he doesn't."

"What does he even win?"

"I don't know she wouldn't tell me. But the fact is whatever it is, to win he has to stay with you, and why not have a little fun."

"You want me to mess with him?"

"Make him suffer."

"There's a reason I loved you for years. Your mind terrifies and excites me."

"Of course it does, I'm amazing."

"By the way what's included in sex?"

"Sorry sweetie it covers everything from hand jobs to penetration."

"Dammit. But still I've never done this before, I am probably more excited than I should be, but who cares." Lydia rolled her eyes at Stiles's glee but she was glad she could help him. It really would be fun to watch Derek suffer for the next 7 weeks.

Stiles stood in front of his mirror and checked himself out. Lydia had taken him shopping and she had bought him a whole new wardrobe. He had tried to tell her no but she had just glared at him and told him that it would all be worth it to make sure Derek never made a bet like this again. So Stiles had a new wardrobe and he looked amazing. He was wearing a fitting black shirt that showed off his leaner body, his jeans looked as though they had been painted to his legs but his ass looked amazing so he decided that it was worth it. Stiles took a deep breath as someone knocked on the door. 19:30. Right on time. Stiles waited until Derek knocked a second time and then answered the door. He beamed at Derek who had seem to stopped halfway through a word as he looked Stiles up and down.

"You okay Derek?"

"Erm…yeah."

"Are you ready to go?" Stiles smirked as Derek finally met his eyes and he seemed to realise what he'd been doing as his ears turned red.

"Yeah. Sorry I was just a little thrown."

"By what?" The innocent act was the best act, according to Lydia. Stiles had his doubts.

"Did you buy new clothes?"

"What these? Oh god no, I just didn't want to do laundry and this was all I had." Derek nodded his head dumbly as he raked his eyes up Stiles legs. Stiles wanted to just let him stare but Lydia had told him that these jeans hugged his ass for a reason and Derek needed to see that. Stiles pushed Derek back a little as he pulled the door closed behind him. He pulled the door closed till he heard it click, then he smiled at Derek and took off down the hallway. He smirked again as he heard Derek give a small whimper, he schooled his features and stopped. He looked over at Derek who was still stood by his door. "Are you gonna come Derek?" Lydia was right. Innocent totally made it sound like an innuendo; Derek blushed and walked after him. Stiles saw Derek rearrange his trousers before he turned around and started walking again.

"So where are we going?"

"I was thinking of a movie."

"Great. I can't wait." Stiles probably looked a little crazy with glee but he really couldn't wait. A dark theatre with Derek, a lot can happen at the back of that theatre. Stiles and Derek walked side by side till they reached the Camaro and Derek opened the door for him and Stiles climbed in. Derek drove them to theatre and they stayed in companionable silence. Derek smiled over at Stiles a few times and he looked happy, if he knew what Stiles was thinking he wouldn't but he didn't so Stiles just smiled back. Derek pulled in to the parking lot behind the theatre and they walked in together. Stiles let Derek pay, since Stiles wasn't going to be watching the film anyway, and then they grabbed two drinks, Stiles got a hot dog and Derek got popcorn and they made their way in to the screen. Stiles beamed as he looked around apart from a couple at the front they were totally alone, he nudged Derek towards the back of the theatre and they sat down. Stiles balanced his hot dog on his knees and then started to pull the bread apart; he needed to eat the hot dog separately. He could see Derek watching his hands as he ate, Lydia had mentioned that he needed to draw attention to his fingers and his mouth, so he did, he ripped up the bread and Derek just watched as he put it in his mouth and the tips of his fingers dragged across his bottom lip. He could see Derek's tongue sweep across his own bottom lip as Stiles sucked the sauce from his fingers. Stiles hadn't even noticed the lights going down or the adverts or the movie starting because he just wanted to see what other reactions he could get out of Derek. Stiles stared down at his lap and had to hold back his own blush because all that was left was the hot dog and either he'd look ridiculous or he'd look ridiculous but Derek would get turned on anyway. Stiles brought it to his mouth and licked at the sauce on the end, he heard Derek take a quick breath and Stiles decided what the hell as he swirled his tongue around it to lick off the sauce. He pushed it in to his mouth and hollowed his cheeks a little. He could hear Derek panting a little beside him and Stiles finished off the hot dog without showing him any concern. Stiles knew he was being a little shit and he should probably quit while Derek was like this but he never did know when to stop and this was going better than expected. Stiles picked up his drink and swirled the straw around with his tongue, he had no idea what was happening on the screen but neither did Derek so it didn't really matter. Stiles put his drink down and decided to go for it so he put his hand on Derek's knee. Derek's eyes followed the movement as Stiles moved his hand slowly further up Derek's leg. Derek sucked in a breath as Stiles hand drifted closer to his cock. Stiles attention was kept on the screen and his face was completely still while Derek practically panicked in the theatre. Stiles hand stopped just at the top of Derek's thigh and Derek released the breath he'd been holding. Stiles smirked before he leaned over to Derek and brought his mouth up to Derek's ear.

"Are you okay?" his breath ghosted over Derek's cheek as he whispered.

"I'm fine."

"Sure about that? You're looking a little flushed." Stiles bent his head a little as he kissed down Derek's neck. He felt Derek swallow and Stiles ghosted his fingers over his clothed cock. Stiles licked at Derek's pulse point and pressed a little more firmly against his cock. Stiles sucked a mark in to his neck and ran his fingers over Derek's full length before he pulled away completely. Derek stared at Stiles as he sat back in his seat as though nothing had happened. Stiles looked at him then gave him a small smile.

"I'm sorry that was unfair of me, to be honest you've seemed sick all night and I should have just made you go home and rest." Derek stared at Stiles with wide eyes and then slowly turned to look at the screen. Stiles couldn't help but feel happy the rest of the film, mission blue balls was coming together. Okay Lydia was right he really needed a better name for this.

They were sat in Derek's car. They had finished the movie, with neither of them really knowing what the hell actually happened in it. Derek didn't know if he was supposed to mention what just happened but Stiles took that decision out of his hands when he started apologising. He apologised again and again, but Derek wasn't sick and now Derek felt guilty because Stiles felt bad for making it worse but there was nothing wrong with him. Derek should just tell him that but Stiles was still talking.

"STILES." He stopped talking. "I'm not sick. You didn't do anything wrong tonight, I'm sorry if I made you feel like that you just threw me off guard."

"Me why?"

"Well the last date we went on you were kind of awkward and now you're like hot tight clothes and touching my dick in the back of a theatre."

"Maybe I'm not as awkward as you think Derek." Stiles leaned forward and kissed Derek. He fisted his hand in his hair and pulled Derek a little further over the middle console. Derek had one arm holding himself up and one holding on to Stiles's hip. They kissed until their cheeks were a little red from the lack of breathing and they were both panting. Stiles placed one more kiss to Derek's lips then winked at him before climbing out of the car. Derek stayed where he was, resting on the middle console as he watched Stiles walk away. Derek swallowed back the drool that was forming because Jesus Stiles ass looked good in those jeans. Derek only pushed himself back in to his seat when Stiles had stepped in to his building. Derek rested his head against the head rest and spoke to the empty car,

"What the hell just happened?"


	5. 29th October

Derek Hale was never the type to give up. He hadn't given up when Laura promised him the Camaro if he was her slave for the whole summer. He hadn't given up when his cousins came to visit for Christmas when he was 19 and wanted to play dress up Derek every day. He was not the type of person to lose but right now he was at a loss because Stiles still hadn't put out and Derek didn't know what was happening. They'd been out on eight dates and every time they got close, Stiles just seemed to lose interest. Derek was set to believe that Stiles just wasn't that interested but then Stiles was grinding down on his lap at the beach and then Derek _knew _Stiles was interested. Now Derek had taken the virginity of quite a few people on campus and he knew he had a name for himself but Stiles would never have agreed to one let alone eight dates if he knew Derek was a notorious one night stand kind of guy. So Derek knew he had to up his game, and not just with the dates because they had been romantic and great, Derek had really gone all out but Derek needed Stiles to know he wanted this as bad as Stiles did. Derek's plan was well thought out and it would have worked if Stiles hadn't panicked and kicked him out of his dorm room. So Derek's great plan was how he now found himself standing in the hallway...naked.

_Three hours before..._

"I'm sorry you're going to do what?"

"The naked man."

"And you thought of this how?"

"I was watching something the other day and this guy did the naked man, apparently it works 3 out of 4 times."

"So you're just going to what...wait for him to turn up and then he'll want to fuck you?"

"That is the plan."

"It's a stupid plan Derek. What if he gets mad?"

"Then I put my clothes back on and give him the puppy eyed apology."

"Uhuh. And if he doesn't want to see you again."

"Erica it's going to be fine. Either we have sex or he gets angry and I beg forgiveness."

"Okay. Do whatever you want. But do not come to me for sympathy because I will either be laughing my ass off in the eyes of your failure or I will be crying because I lost."

"You wouldn't cry! You would probably kick me in the balls."

"Probably."

"Thanks."

"You're welcome, so are you gonna do some manscaping?"

"Why would I manscape?"

"Well you're doing the naked man, I'd hate for Stiles to run because you were looking wild down there."

"Oh my god Erica I am not looking wild anywhere!"

"I'm just saying. Whatever just go and plan or whatever." Derek huffed then turned around and left the apartment. "Good luck." Derek closed the door behind him and text Stiles.

_29.10 19:18pm D to S: Hey, are you free tonight?_

_29.10 19:20pm S to D: I should be. Wanna come over for a movie?_

_29.10 19:21pm D to S: Yeah sure, I'll come over about 10?_

_29.10 19:22pm S to D: Yeah okay._

Derek's plan was off to a good start and he only had a few things left to do before he could really try out the naked man. So he walked to the shop near Stiles's dorm because he definitely wouldn't need his car tonight. He ran inside and bought the essentials, lube, condoms and snacks for afterwards. Some people might say he's being overly confident but Derek knew what he looked like and there was no way he was going to be the 1 out of 4 that it failed for. He got some cash out because no doubt Stiles ridiculous roommate would be there. Matt or something like that, it didn't really matter Derek just needed him out of the room. Derek made his way over to Stiles's building and followed one of the other residents in, she threw a glare his way he'd obviously slept with her before. He rushed past her and jogged upstairs, he knocked on the door and Matt answered.

"What?"

"I need you to leave for the night. I don't care where you go, it just can't be here."

"Wow friendly. What's in it for me?"

"Fifty if you leave right now. Ten if I have to kick your ass first."

"Fifty it is."

"Good choice." Matt ran back in the room and grabbed his stuff before passing Derek, he held out the money and smiled as Matt practically ran away from him. Derek looked around the room and yeah he was going to have to do some serious cleaning, he really wanted the bet to just be over with already.

Derek cleaned everything he could; he even tidied up Matt's side of the room and had arranged all of Stiles things so that everything looked nice. It barely took him an hour so now he was just waiting till Stiles came back. Derek looked at the clock and sighed 20:32pm. Derek pulled all of his clothes off and looked in the mirror. He did not need manscaping, he was perfectly acceptable down there, no one had ever complained. Wait he was going to sleep with Stiles tonight and he hadn't even showered this morning, what the hell was he thinking? Derek contemplated it and then decided to just jump in Stiles's shower; he scrubbed every inch of himself…twice. Give him a break he was a little nervous about this. He dried off and looked at himself in the mirror; he looked good, stupid Erica getting in to his head. He sat on Stiles's bed and read the books beside his bed. At about 3 minutes past 10 Derek could hear someone outside the door. Now in retrospect Derek probably should have thought of the possibility of Stiles bringing someone home, to find Derek stood in the room completely naked with his hands on his hips and a look that he would call his smoulder. So of course that's how Derek had found himself standing in the hallway because of course it was Stiles and Stiles's dad, who had instantly pulled a gun because he thought Derek was a pervert or something. Now Derek will deny the squeal he made to his dying day, because in seconds everything was chaos, Stiles was screaming at his dad to put his damn gun down, his father was telling Derek to leave the room and so Derek had found himself cowering in the hallway with orders to not move, so now he was standing by the door with just his hands to cover his junk. Derek dropped his head on to the door and just thanked every god out there that he hadn't pissed himself. He turned his head when a brief flash of light came from beside him.

"Did you just take a picture of me?"

"Yes."

"Why?"

"You're Derek Hale."

"Thanks but I know my own name."

"This is for your website."

"My website?"

"Well it's more of a blog on tumblr."

"What are you talking about?"

"How do you not know about it?"

"Can you do me a favour, and start from the beginning?"

"Fine. About a week ago someone created a blog called One Hale of a Night Stand, I'm assuming it's someone you slept with and never called but who knows, and basically everyone you ever slept with follows it and reveals their experiences."

"You cannot be serious."

"Seems you pissed off the wrong person."

"Well I know I've never slept with you, so delete the picture."

"No but you did sleep with two of my best friends with the promise to call. Think of this as my revenge on their behalf."

"Who the hell are you?"

"Heather. And by the way Stiles is one of my close friends, and you just met his dad, now if you hurt him Stiles won't tell his dad but I will and believe me he will kill you and I will help."

"I'm not gonna hurt him Heather."

"For your sake I hope not." Heather smiled at him and turned on her heel.

"What about the photo?"

"What about it?" Heather disappeared behind one of the doors and Derek didn't think his night could get any worse but then Stiles door opened. Stiles was standing there with his clothes, his dad behind him with a glare that could rival Derek's mothers. Stiles pushed Derek's clothes in to his arms and then moved in to the hallway closing the door behind him.

"What the fuck were you thinking?"

"Why is your dad here?"

"Derek this is not the time for your questions, why were you fucking naked in my room?"

"I was doing the naked man."

"The naked…from How I Met Your Mother?!"

"Yeah."

"I'm going to fucking kill you! How was that ever a good idea?"

"I'm sorry! Okay I am so sorry but I didn't exactly think 'Hey maybe Stiles will be bringing his dad for movie night!'"

"Don't you check your fucking phone! I text you to tell you we had to cancel because there was a mix-up at the hotel and my dad's room won't be ready till tomorrow."

"Oh…"

"Yeah. Would you please get fucking dressed?" Derek dropped his clothes and quickly started pulling everything on.

"Look this is really not how I usually go about meeting people's parents, and I am so sorry for this. Let me make it up to you?"

"Well it's not like I planned for you meeting my dad, he's the Sherriff back home and I guess around Halloween he worries about me getting caught up in…I don't know actually but whatever. You didn't exactly help with the nakedness."

"You didn't want me to meet your dad?"

"That's what your focusing on, anyway why would you this is only a b…beginning of a relationship. We don't even know what's going to happen, so obviously I didn't want you to meet him yet."

"Right, obviously. So how long is he staying?"

"Just the weekend. Call me Monday?"

"I will call you Monday." Stiles pressed a quick kiss to Derek's lips then went back in to his room. Derek huffed and started walking home.

When Derek pushed the door open to his flat he could already hear Erica's cackling form the living-room. He rounded the corner and as soon as she saw him she burst in to more fits of laughter, he looked to Boyd for help but the usually stoic man was doubled over. Derek looked around helplessly until Isaac came out from the kitchen. He saw Derek and his mouth split in to a huge grin.

"Derek, I am so glad I know you. Without you I would lack a serious amount of entertainment in my life."

"What is happening?"

"You ever heard of One Hale of a Night Stand?"

"Surprisingly it has been mentioned tonight, what the hell is it?"

"Well look for yourself." Isaac gestured towards the laptop on the couch and Derek picked it up and sat down. Derek's eyes nearly bugged out of his head as he took in the page. The background was the picture that Heather girl had taken earlier, he was completely naked standing outside Stiles door, and there was post after post about him. Down the side there was small profile pictures and the ones that used their actual picture Derek recognized and as he scrolled down, it seemed that just about everyone he'd ever slept with was following this person. As for the person who ran the blog, there was no details given about them and they'd used a picture of Derek's face with devil horns drawn on to it.

"What…"

"Derek, seriously who the fuck did you piss off?"

"I don't know."

"They even have a rating system dude. It goes from as Hot as Hale to What the Hale was he thinking?"

"What the Hale was he thinking?"

"That one seems to be used the most when you have drunken night stands, what the hell do you do when your drunk Derek?"

"Erm…" Erica tried to straighten up but she really couldn't look at him without doubling over again. She clutched her sides as she laughed and continued to laugh as she rolled right off the couch.

"Is she going to be okay?"

"Yeah, I'm the one that found the blog so I had my fill earlier. Dude I had no idea you were this well known."

"I am going to kill whoever did this." Derek set the laptop down and stormed in to his room. He heard Isaac shout after him before he closed the door "Where did that picture come from?" Derek closed the door and stripped off his clothes. He laid on his back and thought about who would be pissed enough. He didn't really think any of his one night stands would be mad enough, he never really promised them anything, and honestly he figured the only person that would be pissed is Stiles. If Stiles ever found out about the bet then yeah Derek could see him being angry enough to do something like this but Stiles didn't know about it. Derek hated it, hated that the whole reason he had the nerve to ask Stiles out was because he got something out of it. He scrubbed his hands over his face and closed his eyes, yeah he was an ass for making the bet but Stiles would never know about it and Derek could pretend like he asked Stiles out because he got some courage.


End file.
